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Synonym name: Donaxine; Doranine
Catalogue No.: BP0689
Cas No.: 87-52-5
Formula: C11H14N2
Mol Weight: 174.247
Botanical Source: Alkaloid from Arundo donax, Phalaris arundinacea, some Lupinus spp. and barley shoots. Also from Acer saccharinum, Acer rubrum, Brassica oleracea and Desmodium pulchellum
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams.
For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.
HPLC of Gramine
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
19.0300
2.3085
.5185
3.0125
2.5476
24.8463
High
49.6783
1.8366
Yes
Yes
No
No
No
Yes
0.6
No
No
Yes
No
Gramine, also known as Donaxine, is a naturally occurring alkaloid that was first isolated from plants of the genus Gramine. As a small-molecule natural product, reed basal has attracted widespread attention due to its multi-target biological activity. In recent years, as the important role of adiponectin receptors (AdipoR) in metabolic diseases and inflammation regulation has gradually been revealed, olealine, as an effective adipoR agonist, has demonstrated unique pharmacological potential. Additionally, olebagin's activation of β2-adrenergic receptors (β2-AR) gives it potential value in nervous system and immune regulation. Extensive studies have shown that olebaline has significant anti-tumor, anti-anti-inflammatory, and antiviral activities, involving multiple signaling pathways and molecular targets, indicating broad prospects as a candidate molecule for novel drugs.
This paper systematically reviews the chemical structure and physicochemical properties of ole bamboo aline, plant origin and extraction methods, pharmacological activity, and mechanism of action. Combining druggability evaluation and pharmacokinetic characteristics, it explores its clinical application prospects and future research directions, aiming to provide theoretical basis and research references for the pharmacology of natural products and related drug development.
The chemical name of luzhuzaline is N,N-dimethyl-3-indole-methylamine, with the molecular formula C12H14N2 and a molecular weight of 174.2470. Its structural core is an indole ring system, connecting an N,N-dimethylamine side chain, with a simple structure but diverse functions. The LogP value of luzhaline is 2.3085, indicating moderate lipid solubility, which facilitates cell membrane penetration and distribution in vivo. The topological pole surface area (TPSA) is 19.03 Ų, and the lower polarity helps with its blood-brain barrier (BBB) penetration capability. Experiments have confirmed its high BBB permeability, suggesting its potential application in central nervous system diseases.
The water solubility index is 3.0125, indicating a certain degree of water solubility, which is beneficial for absorption and distribution in the body. The hERG channel inhibition test was negative, indicating a low risk of neophylline cardiotoxicity. The Ames test result was 0.6, indicating a low genotoxicity risk and a solid safety foundation.
In summary, the physicochemical properties of ole alkaloid meet the basic requirements for drug development, while it also has good bioavailability and safety, making it a natural product with promising drug potential.
Arundo is mainly found in the genus Arundo and related Poaceae plants, such as Phragmites australis and Arundo donax. Its content varies depending on the plant species, geographical environment, and growth stage. Traditionally, extraction of reed bamboo soda mostly uses alcohol solvents (such as methanol, ethanol) to extract dried plant materials, combining acid-base extraction with liquid-liquid distribution technology to obtain high-purity reed bamboo aline.
Modern extraction processes are moving toward green and environmentally friendly practices, with ultrasound-assisted extraction, microwave-assisted extraction, and supercritical fluid extraction methods gradually being applied to improve extraction efficiency and purity, while reducing the use of organic solvents. After extraction, column chromatography (silica gel, C18 reversed phase column) and high-performance liquid chromatography (HPLC) technology were used to separate, purify, and quantitatively analyze reed bamboo alkaloid to ensure its quality stability.
Moreover, with the development of synthetic chemistry, olealine can also be obtained through chemical synthesis, providing a foundation for large-scale production and drug development.
As an effective agonist of adiponectin receptors AdipoR1 and AdipoR2, olebaline has IC50s of 4.2 μM and 3.2 μM, respectively. Adiponectin receptors play a key role in regulating energy metabolism, insulin sensitivity, and inflammatory responses. By activating AdipoR, reasine promotes the activation of AMPK and PPARα signaling pathways, improves lipid and glucose metabolism abnormalities, and demonstrates potential anti-diabetic and anti-obesity effects.
Oleazine has an agonizing effect on β2-AR in mice and humans, which plays an important role in bronchiectasis, cardiovascular regulation, and immune response. By activating β2-AR, doperine regulates smooth muscle relaxation and immune cell function, and may have therapeutic potential for asthma, chronic obstructive pulmonary disease (COPD), and immune-related conditions.
Olebaline exhibits significant anti-inflammatory activity, targeting key inflammatory mediators and signaling molecules such as IL-6, STAT3, CASP1, TRPV1, PTGS1, TNF, TRPA1, NOS2, PTGS2, and NFKB1. Research shows that olebambooline can inhibit the expression of pro-inflammatory cytokines (such as IL-6, TNF-α), block the NF-κB and STAT3 signaling pathways, and reduce inflammatory responses. Additionally, the regulatory effects of doperine's TRPV1 and TRPA1 channels help alleviate inflammatory pain and neuroinflammation.
Olebaline exhibits effects in inhibiting cell proliferation and inducing apoptosis in various tumor cell lines. Its antitumor mechanism involves regulating the cell cycle, activating apoptotic signaling pathways (such as CASP1-related pathways), and suppressing the tumor-related inflammatory microenvironment. Some studies have indicated that olebaline activates adiponectin receptors, regulates tumor metabolism, and inhibits tumor cell growth and metastasis.
Dolu alkaloid exhibits inhibitory activity against various viruses and may act by interfering with viral replication cycles and regulating host immune responses. The specific mechanisms require further research, but their ability to regulate inflammation and immune pathways provides theoretical support for antiviral effects.
The multi-target mechanism of olebamine reflects its complex pharmacological characteristics. As an agonist of AdipoR1 and AdipoR2, oleazine promotes activation of the adiponectin signaling pathway, enhances the downstream effects of AMPK and PPARα, and regulates energy metabolism and inflammatory responses. AMPK activation not only improves metabolic disorders but also inhibits NF-κB-mediated inflammatory responses, forming a dual regulation of metabolism and inflammation.
In terms of β2-AR stimulation, olebaline activates adenylate cyclase through Gs protein-coupled receptors, boosts intracellular cAMP levels, regulates smooth muscle relaxation and immune cell function, and exerts anti-inflammatory and immunomodulatory effects.
Lutealin is especially crucial in regulating inflammation-related targets. It inhibits the expression of IL-6 and TNF-α, blocks the STAT3 and NF-κB signaling pathways, and reduces the release of pro-inflammatory factors. Regulation of CASP1 affects pyroptosis and inflammatory cascade responses, while regulation of TRPV1 and TRPA1 channels involves pain and neuroinflammation relief. Additionally, olebaline inhibits PTGS1/2 (COX-1/2) and NOS2 (iNOS), reduces the production of prostaglandins and nitric oxide, and further alleviates inflammatory responses.
Overall, oleazaline achieves multiple anti-inflammation, anti-tumor, and antiviral effects through the synergistic effects of multiple targets and pathways.
Olebaline has a moderate molecular weight (174.2470 Da), which complies with the Lipinski rule and is beneficial for oral absorption. LogP values (2.3085) and TPSA (19.03 Ų) indicate good lipophilusibility and membrane penetration, especially its high blood-brain barrier permeability, offering potential for treating neurological diseases.
Moderate water solubility (3.0125) supports good distribution and absorption in the body. Negative hERG channel suppression suggests a lower risk of cardiotoxicity and better safety. Ames test results (0.6) indicate a low genotoxicity risk.
Pharmacokinetics, olealine is rapidly absorbed orally and widely distributed in the body, especially entering the central nervous system. Its metabolism mainly occurs through the hepatic enzyme system, and the metabolites require further identification. Excretory pathways include kidney and bile excretion. It has a moderate half-life and supports relatively flexible dosing regimens.
Currently, systematic pharmacokinetic research on olebaline is limited. Future studies on metabolic kinetics, toxicology, and drug interactions need to be strengthened to improve its druggability evaluation.
As a multi-target natural product, olebambooline has broad clinical application potential. Its properties as a adiponectin receptor agonist give it potential therapeutic value in metabolic diseases such as metabolic syndrome, type 2 diabetes, and non-alcoholic fatty liver disease (NAFLD). By regulating energy metabolism and inflammatory responses, aspergine is expected to improve insulin resistance and related complications.
Its β2-AR agonist action offers new therapeutic approaches for respiratory diseases such as asthma and COPD. Anti-inflammatory and antitumor activities open new directions for inflammatory diseases and tumor treatment, especially with potential applications in tumor microenvironment regulation and tumor immunotherapy.
Its antiviral activity suggests the development potential of olebasine in viral infections and related immune regulation, especially in the current context of frequent viral diseases worldwide, which is of great significance.
However, the clinical application of luzhalin still faces many challenges, including unclear pharmacokinetic properties, insufficient long-term safety data, and insufficient clinical validation of efficacy. In the future, systematic preclinical and clinical studies should be conducted to optimize dosage forms and dosage regimens, clarify indications and treatment windows.
In addition, by integrating modern drug design technologies and developing structural modifications and drug carrier systems, the targeting and bioavailability of olebaline will be enhanced, further promoting its clinical translation.
As a natural alkaloid with multi-target effects, doperine, due to its agonistic activity of adiponectin receptor and β2-adrenergic receptor, exhibits various pharmacological effects including anti-inflammation, anti-tumor, and antiviral effects. Its excellent physicochemical properties and safety have laid a solid foundation for drug development. In the future, with further in-depth research into its mechanisms of action and pharmacokinetics, oleuminine is expected to become an important candidate drug in the fields of metabolic diseases, inflammatory diseases, and tumor treatment.
Systematically integrating the pharmacological research results of olebaline and combining it with modern drug development technologies will provide valuable theoretical support and practical experience for the advancement of natural product pharmacology and new drug development. We look forward to the greater value of oleazine in clinical applications and its benefit to human health.
Shenshuai
Wenjing
Hedandan
